Mr. Dickey was a faculty member of the UW-Madison Law School from 1976 until his retirement in 2011. He was Evjue-Bascom Professor from 1997-2007, when he was awarded the George H. Young Chair. He has served as the faculty director of the Remington Center for Research, Education and Service in Criminal Justice since 1975. Now staffed by 17 full time clinical faculty, the Center includes projects in Restorative Justice, Appeals, Legal Assistance to the Institutionalized, Prosecution, Defense, Innocence, Family Law and Economic Justice. The Center has provided thousands of law students with the opportunity to provide service, do research and gain experience in criminal justice.

Mr. Dickey led the Division of Corrections from 1983 to 1987, and in an earlier leave of absence from the Law School drafted its Administrative Rules. He has been a member of the American Law Institute since 1989 and chaired the Governor's Task Force on Sentencing and Corrections, which reported in December 1996. He was a member of the Executive Sessions on Sentencing and Corrections, sponsored by the U.S. Department of Justice. He chaired the UW Athletic Board from 2005-11, and had been a member since 2003. Prior to chairing the Board, Mr. Dickey served as the UW-Madison Faculty Representative to the Big Ten, WCHA, and NCAA.